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Total Synthesis of (−)‐Merochlorin A
Author(s) -
Brandstätter Marco,
Freis Manuel,
Huwyler Nikolas,
Carreira Erick M.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813090
Subject(s) - total synthesis , aldol reaction , cycloaddition , chemistry , aromatization , stereochemistry , aldehyde , enyne , sequence (biology) , enol , bicyclic molecule , tandem , combinatorial chemistry , catalysis , organic chemistry , biochemistry , materials science , composite material
The first asymmetric total synthesis of the meroterpenoid (−)‐merochlorin A is described. The route features enantiospecific gold‐catalyzed tandem 1,3‐acyloxy migration/Nazarov/aldol reaction sequence to furnish the bicyclo[3.3.0]octane core in a single step from a linear propargylic 1,3‐enyne aldehyde. After completion of the central skeleton by reductive enol lactone rearrangement, late stage Diels–Alder cycloaddition/aromatization sequence installed the resorcinol. An additional salient feature of the synthesis is the assignment of the absolute configuration, which had not been determined previously.